Water → HCID 66701588, compound

HRID 1186769Notes

Reaction equation

HRID 1186769 reaction equation
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH3:18])[C:12]=2[N:19]([C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[OH2:35].C[N+]1([O-])CC[O:40]CC1>CC(C)=O.O=[Os](=O)(=O)=O>[OH:35][CH:2]([CH2:3][OH:40])[CH2:1][C:4]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH3:18])[C:12]=2[N:19]([C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:9])=[O:8])[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxide2×HCID 66701572HCID 66701572, compound

Product 1

HCID 66701588HCID 66701588, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalyst2×HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (3-{[(1-allylcyclopropyl)sulfonyl]amino}-1-methyl-6-oxo-1,6-dihydropyridin-2-yl)(2-fluoro-4-iodophenyl)carbamate (180 mg, 0.298 mmol) in acetone (20 ml) was added water (3 ml). The mixture was cooled to 0° C. and 4-methylmorpholine N-Oxide (7.36 eq, 257 mg, 2.195 mmol) was added, followed by OsO4 (2.5% w.t. in t-butanole, 111 μl). The mixture was stirred a room temperature for 18 hours. Since the reaction was not complete, more 4-methylmorpholine N-Oxide (6 eq, 210 mg, 1.790 mmol) was added, followed by OsO4 (2.5% w.t. in t-butanole, 110 μl). The mixture was stirred a room temperature for another 18 hours and then concentrated in vacuo. The residue was diluted in ethyl methyl ketone and washed with water. The aqueouse phase was separated and extracted twice with ethyl methyl ketone. The combined organic layers were washed once with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound (177 mg, 93%).

Workup

  1. stirringThe mixture was stirred a room temperature for another 18 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted in ethyl methyl ketone
  4. washwashed with water
  5. customThe aqueouse phase was separated
  6. extractionextracted twice with ethyl methyl ketone
  7. washThe combined organic layers were washed once with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-05c3ea39945545d3b017232df1f8a8a0
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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